In 1956, Andy Warhol began creating a series of holiday-themed drawings for Tiffany & Co. in New York City. These drawings ranged from angels to whimsical Christmas trees and ornaments to drawings of shoes. The first Warhol Christmas card, Butterfly Tree, was published in Tiffany's 1956 catalogue, bearing a caption that read "Gay cards with Christmas spirit".  Tiffany & Co. continued publishing Warhol's illustrations as Christmas cards until 1962.

A Whole Stocking Full of Good Wishes was created around the same time as Warhol's work for Tiffany's, and features the signature script of Julia Warhola. "Shoes made a nice Christmas image. St. Nicholas, as legend has it, threw gold coins in the window of three sisters who needed dowries to marry; the gold coins landed in their shoes (which also explains Christmas stockings).

Warhol's enthusiasm for both Christmas and shoes can be traced throughout the decades. This piece brings together both of these loves, and offers Warhol's holiday wishes for the kind of Christmas he perhaps never had.